Shift To Managing 100% Remotely Like A CHAMP — Use These Questions To Guide You

I have a confession: I like being around people I work with, in close proximity in the same physical space. And I have been feeling a lot of the pains, stresses, and challenges of becoming a fully-remote Leader & People Manager. It’s a shift that I wasn’t ready to make, but fortunately a shift I’ve prepared myself to make successfully.

And if you are a Manager, or a Team Lead, or an Executive who is suddenly faced with leading a completely remote or distributed team, then you might be feeling some of the same pressures and challenges. 

So in this post, I want to cover a handful of valuable questions that you can use so that you can also make this shift. By doing so, you can truly  become a real champion at leading individuals and teams in a remote environment. 

As I write this, we’re in the midst of a global pandemic, and on top of all of the horrible health crises that are going on, the economy is also taking a huge hit. 

So many companies are experiencing a ton of layoffs. 

Many businesses have slowed down or completely shut down their operations.

And also, there remain many companies who are still engaged in their day-to-day operations. And for those who still are engaged in the day-to-day operations, your dynamics in the workplace have completely shifted. They’ve dramatically shifted. 

And those of you in leadership roles might feel a little bit like fish out of water, because you’re not used to how to handle this new normal where you’re trying to manage people who are working at home, living at home, really trying to survive and trying to thrive in this new dynamic. 

You might be asking yourself, “How can I be an effective leader in these conditions where everybody is remote?”

And y’know, I’ve thought a lot about how best to write this post, knowing that everybody is going to have varying degrees of comfort working in remote conditions with remote team members.

Personally, I’m coming from an environment where I’ve had some people colocated on-site in the same office, as well as some people remote. And now, I’m personally in an environment where everybody is remote, and everybody is completely separated and isolated from each other, at least physically. 

Other readers may have never experienced this before. 

Still others may be completely comfortable in an all-remote situation. 

So, because everybody’s going to have varying degrees of comfort working in an entirely remote situation

Rather than pretend like I have all of the answers…

And rather than pretend like I can tell you exactly what to do given your unique situation… 

Instead, I’m going to provide you with a series of questions that — if you can ask yourself and answer HONESTLY and TRUTHFULLY to the best of your ability — will really help you to thrive and make this shift and show up like a true champion. 

So given that context, let’s go ahead and jump in with the first of five questions that I know will really help you make the shift to becoming a Remote Management CHAMP.

Question 1: Are My People Pointed In The Right Direction?

So the first question to honestly, truthfully answer for yourself is, “Are my people pointed in the right direction?” 

Are they clear about what they should be working on and what it is that they’re working towards? 

This is question #1 because it can be really, really easy to get distracted right now as people are adjusting to this shelter-in-place, work-at-home environment, especially if they’re not totally used to remote work. 

Personally, I’m getting all the pros and cons that come with living alone (aside from my little terror 8 month old golden retriever puppy), but a lot of people have a ton of other things going on at home. 

They’ve got kids who are at home who are doing remote schoolwork. They’ve got their spouses at home. They’re trying to juggle their spouse’s work schedule with their work schedule, and conflicting meetings etc.

OR, maybe they have a spouse who is unemployed or partially employed. 

They might have pets and kids and spouses and all these other things that they’re trying to juggle. So it’s really super easy to get distracted just by that situation alone, where everybody is kind of cooped up at home and they’re all trying to deal with each other now 24/7 as opposed to just a fraction of each day. 

On top of that, you’ve got all the comforts of home, which I often refer to as all of the available distractions of home. You have your Netflix, your video games, your laundry, your house projects, dirty dishes… all of these other things which can easily become distractions.

So, all these aspects of this new situation make it hard enough already right out of the gate. On top of that, then, the reason you wanna ask, “Are my people pointed in the right direction?” is because it’s entirely possible they have multiple work-related things on their plate. So you need to ask yourself if they know whether there’s a clear priority order on those things. Literally nothing kills productivity like context switching and conflicting priorities. 

So be honest: is there clarity on what thing is the most important thing in any given week, month, day even. If you DO have that clarity with your people and a shared understanding on the priority of things, then that means they don’t have to enter each day guessing. They know that they’re pointed in the right direction, that what they’re working on is the most important thing, and that they are moving in the right direction. No guesswork necessary.

Question #2: Do My People Understand What Success Looks Like?

So, if the first question is whether people are focused on the right things, the next question to answer honestly is, “For what they’re working on, do my people know what success looks like?”

At the end of the day, our people — especially the high achievers — need to know how to win. So: How do they win?

What are the goals for what it is they’re working on? 

Obviously, their work isn’t there just to keep them busy, to have activities and tasks for them to do. They need to understand what success looks like. What does it look like when they win? What are the goals of what it is they’re working on? 

Are there any metrics or clearly defined parameters for success of what they’re working on? There are a lot of different models & frameworks that different companies use to define success, and while I won’t go through all of them, I’ll pick one to illustrate: The OKR model.

OKR stands for Objectives and Key Results. So the objective might be a description of they’re working towards, and the key results are the metrics or the other clear indicators of success that they’re contributing to. 

And this question is multi-faceted, because what you really want to ask is two questions:

“Do my people fully understand what success looks like?”

“Do I as a leader communicate what success looks like to my people regularly and repeatedly?”

So again, be honest with yourself (no judgment here on the blog): Do you communicate the keys to success? Do you communicate and paint a picture of what success looks like on a regular basis? Do you repeat yourself, and have you actually gotten comfortable repeating yourself? 

Y’know, one of the most surprising lessons I ever learned as a leader was that I had to get comfortable repeating myself. In my early years, I would get frustrated when I’d say something one time and then find out that people didn’t pick up when I was putting down, so to speak. And it was honestly kind of aggravating until I realized that people are at-best going to listen to what I say and take away 1 or 2 things at any given time. 

So, I needed to be able to repeat the message until everybody heard the things I needed them to hear. Truth of the matter is that this may take two, three, four, five, ten times repeating things like the metrics for success before it actually stuck with everyone.

Once you can confirm that you are communicating the parameters for success repeatedly and on a regular basis, a next step could be to go beyond just broadcasting this information and asking, “Are these things written down somewhere? Are they documented somewhere where people can easily find them?” 

This is a huge time- and energy-saver, especially for somebody like myself who still is not totally comfortable repeating myself over and over and over again. I find that it’s much easier on everyone when people can also pull this information from somewhere. That way, they’re not relying on me to constantly push it out to them and broadcast it all the time. So, by making it so that people can quickly find this information and easily reaffirm what success looks like for them, you’ll be even better off.

And I’d like to take a quick moment to call attention to a blindspot a lot of us leaders fall prey to: just because you as a leader/manager/executive know what the parameters for success are, that does not mean that all of your people on your team naturally know those things. 

It’s all too easy for us as leaders to forget that we’re involved in conversations that people on our teams are not involved in, and we’re probably involved in establishing goals, determining the best metrics, setting these key results. Most likely, your entire team is not a part of that decision-making process. And that has a huge, huge potential to create a disconnect. 

So if you can’t confidently answer “Yes” to this question, I would ask you, “Can you put together a clear mission statement for whatever it is that your people are working on, with clear, unambiguous measures for success?”

Here’s a couple hypothetical examples:

Software Engineering Example

So let’s say your business is an eCommerce platform, and you’ve got a mobile app. And your team is focused on helping users to more easily manage their orders from a mobile device. So you might tell your Engineers that the Objective is to deliver better order search with improved sorting and filtering features this quarter (best to make it somewhat time-based).

And then we might put some metrics on adoption of what they’re developing to determine the success of this objective: 

Success = 10% of active mobile users are using these features in the first week after we launch

Customer Success Example

For a non technical example, let’s switch gears to Customer Service / Customer Success. 

Let’s say your high-level objective is to ensure that your customers feel like they’re heard, and feel like you’re responsive to their requests. 

So you might set metrics to that similar to the following:

Success = average first response to customers’ email inquiries no higher than 12 hours after they email on weekdays.

To add to that, we might also say:

Success = No more than 5% of those first-response emails from Customer Success to occur outside 24 hours of the customers’ email. 

The key here is to be extremely thoughtful about the metrics we choose and not just saying, “Here’s a vague, ambiguous objective”. And I can’t stress enough that the more time and thought you can put into establishing those metrics, those key results, the better off you’re going to be. The more specific those metrics are, the better. Otherwise you end up with people chasing the wrong metrics, which puts every objective at risk.

Question #3: Do My People Know What The Stakes Are?

Put another way: “Do my people know why the things that they’re working on are important?”

Do they know what the impact of their work is for your customers? 

Do they know what the impact is for the company

Do they know what the impact is for their colleagues? 

Do they know if & how their work ties into other projects, goals, or initiatives? 

Do they know if their work is a dependency for other work to get started? Do they know if their work is a dependency for unlocking further progress on other work? 

Do they know if their work is a dependency for other work to be completed?

And perhaps the biggest benefit of clearly articulating the stakes? it really builds in automatic accountability mechanisms that are far, far, far more valuable and far more effective than some manager looking over their shoulder constantly. In case you haven’t noticed, that is basically impossible to do right now. Try taking laps around the office and looking over their shoulder. I’ll wait here 🙂

And even more so than success metrics, remember that just because you know what the stakes are doesn’t mean that they know what the stakes are. 

Consider that most people at an individual contributor level — your customer success reps, your software engineers, your marketing associates, your warehouse staff — most of these folks are going to be laser focused on their piece of work, their tasks, their contributions.

Even if they heard through the grapevine how this all plays into the bigger picture, and all the things that it impacts, they might’ve forgotten by now because they are so focused on getting their work done.

And once again, just like you, your peers, all of humanity: everybody has a ton of things on their minds right now, in particular non-work things. They’re trying to get kids set up for online school, and they’re trying to figure out how and when they’re going to go to the grocery store, and they’re figuring out like what they’re going to do about their elderly parents who don’t live nearby. They’ve got a lot on their minds. 

So just because you remember the bigger picture doesn’t mean that other people know the bigger picture or have it in the front of their mind. And it really doesn’t hurt anything to remind them by painting a clear picture of what the stakes are.

Question #4: Am I Checking In Using The Right Cadence & Frequency?

Question #4 might be a bit of a contentious one, and if you tend to micromanage this may get a little uncomfortable: “Am I checking in with the RIGHT cadence/frequency?”

For any leader, it’s important to check in and make sure that things aren’t going completely off the rails. You’ve got your people pointed in the right direction, with a clear understanding of success and what the stakes are for their work?

We want to make sure that people are focused on the right things, not the wrong things, and they have their priorities in order, that they understand the bigger picture, the goals, the stakes, all of those things. 

And while I don’t know your exact workplace culture, I would suggest that in most scenarios as a manager, daily check ins right now are probably going to be a little too frequent. 

It’s going to start to feel a little micromanage-y if you check in with people on a daily basis how things are going. There are definitely cases where daily check-ins can be valuable, but just based on how variable everyone’s productivity can be right now, and given the shelter-in-place conditions, it’s probably too frequent. 

Look: IF you’re used to micromanaging, I’m really glad you found this post, but I want to warn you that people who try to stick to micromanaging are going to have a really hard time right now, and so I would urge you to try to take this as an opportunity to try a new approach. I can guarantee you micromanaging will not be effective in these stressful, unfamiliar conditions, and it’s going to just end up frustrating you and the people on your team.

So if daily is too frequent, then what should you do instead? Honestly, for conditions like we’re in right now during COVID, I would recommend checking in on progress weekly or 2-3 times per week just to see

• How things are going
• What’s going well
• What challenges they’re facing
• What things could get in their way
• How you could help move things out of their way. 

And I’d like to pause a moment to dive a little deeper on that fourth bulletpoint: 

What things could get in the way. 

If I’ve learned anything over my short 10ish years in leadership roles, it’s that I am most effective as a leader when I’m able to anticipate obstacles that may come up. No, that doesn’t mean becoming paranoid, just anticipating realistic obstacles that could come up… as opposed to reacting to things as they do come up. 

This is especially true when face to face communication isn’t an option. If fires start and you’re trying to help people put out fires via email or Slack or something like that, you’re not able to be nearly as effective as a leader as when you’ve prepared for the potential fires, where everybody even kinda knows what to do in those situations. 

Question #5: Am I Available For My People To Reach Out?

This last question really is going to wrap things up in a lot of ways: “Have I made myself really available for my people to reach out?”

Do they know that you’re available to reach out when certain objectives appear to be at risk?

Do they know that you’re available for them to reach out when they need to brainstorm or bounce ideas off of somebody?

Are you really available when they need to ask questions or get clarification?

And lastly — maybe most importantly during times like this — are you really available for them to reach out when they just need to connect with another human being? 

Y’know, something I’ve tried a handful of times which I feel has been very successful is to occasionally just hold open office hours online. I’ll post a link to a Google Meet or Zoom Meeting, and I continue working heads down on a couple of my own priorities. Inevitably a handful of people from my teams might pop in, often just the chat. Sometimes it’s just for five minutes, sometimes for 20 minutes. One conversation recently was closer to 45 minutes, and I fully enjoyed each of them. 

In each instance, I felt like I was really strengthening the connection that I had with some of these folks — a stronger connection that will build stronger trust among other things — and all this during a time when people tend to feel more isolated and less connected. 

And hey, I’m not suggesting you act like their therapist. All I’m suggesting is to show up and care about the human beings behind the talented employees that are helping you to hit your business objectives. 

And so I think that puts a nice bow on things, because one of the most important distinctions during a time like this is not to focus on just manipulating different pieces on the game board. How effective your teams are — and how effective you are as a remote leader — will largely be attributed to how well you connect with your people. When there are life-threatening elements at play, it’s not just about how you get clear with everybody on the work and the goals, but also how you’re all doing as human beings during such a challenging time.

Wrapping Up

In closing, I know that this whole remote leadership thing might be really new to you, and you might be feeling a bit uncertain or worried that you won’t be as effective as you once were. 

And yeah, the truth is that adjusting your approach to how you manage in different conditions feels a lot like learning a new skill. And at the early stages of that learning process, you might sometimes feel like you suck at it. It will sometimes feel really like you’re treading into uncharted waters, and it can feel like you suck. 

So I’ll leave you with one of my favorite quotes from the TV show Adventure Time: “Dude, sucking at something is the first step to being sorta good at something.”

We all have to start somewhere, and maybe that place for you right this second feels like sucking at it. In the end, though, I know that just by you reading this that you’re dedicated to getting this right, and I want you to know that you got this. 

I know your persistence and your commitment to just making progress progress — not to suddenly mastering this and being perfect at it — is what’s going to get you where you really want to be. So just commit to making regular progress on this, and I think you’ll find that you surprise yourself. 

So in closing, if you plan to use one or all of these questions I’ve covered, I would love for you to let me know which ones in the comments.

Also, if you have any other questions or tools you use to help you along this path, I’d love to hear about those in a comment! 

And lastly, if you think somebody you know would love this or find it helpful, please share it out because through this pandemic and all the challenges that follow, I know that we can continue to help one another  thrive & succeed by simply giving as much as we can. Sharing and helping is our way through this and out of it.